Talk:Aldol reaction

Mistake in translation (Aldol reaction vs. reactions)

It's seems like there might been a slight mistake in translation within the formation of this article, for this reason I propose a split.

Within English, Aldol reaction (singular) refers largely to Aldol addition specifically. While in other languages it seems to be referring to the general set of reactions. For this reason I propose a split to prevent confusion among the average Wikipedia reader.

One for addition that stays this page and is renamed to Aldol addition, because of it's preexisting links to other pages as addition (and because most, but not all, of the page is referring to aldol addition).

And a new one called Aldol reactions. With some of the sections here being moved to it where necessary. LoomCreek (talk) 23:48, 19 April 2023 (UTC)

@LoomCreek This has in the past been a WP:FEATURED article. As such, I think there needs to be a broad consensus for the split you are proposing, since there is clearly potential for confusion given that (if your split were fully accepted) there would be articles at Aldol reaction, Aldol reactions and Aldol condensation, with considerable overlap, for example of mechanism. I think that you need to consider whether your proposal fits with the guidance at WP:SPLIT and allow other interested editors to comment. Mike Turnbull (talk) 14:45, 21 April 2023 (UTC)

@Michael D. Turnbull Okay, I understand that. I will add that there is significant precedent from other language wikipedia's in terms of separate articles. My major issue is that leads to conflicting edits on the page between English speakers and those who are fluent in English but its not their first language. LoomCreek (talk) 14:48, 21 April 2023 (UTC)

@LoomCreek I can see the potential conflicts but I think that we need to proceed carefully and only after consensus so that we are clear what content belongs in each article. Your current request at Wikipedia:Requested moves/Technical requests to rename this article Aldol addition may be a valid way forward but please hold off doing that until others have had time to comment. Mike Turnbull (talk) 14:59, 21 April 2023 (UTC)

@Michael D. Turnbull I will be more cautious in the future. It was just a fairly glaring error in my opinion. And I didn't really expect for this move to have any controversial aspects to it. I'll also adds it's a former GA, not current, while it previously met the standards it no longer does, so it's not necessarily merited any extra protection. I also have done the work to distinguish the content that belongs in each article. LoomCreek (talk) 15:02, 21 April 2023 (UTC)

Everything on this page (with exception for: the stereochemistry section to provide context, a brief comment in the mechanism section to explain how to avoid condensation) is an aldol addition reaction. LoomCreek (talk) 15:32, 21 April 2023 (UTC)

@Michael D. Turnbull

Personally I think Aldol reactions (which I made before I realized the contested nature, if discussion disagrees Ill manually revert it.) should exist but only as a overview page on basics but nudges the reader to go to either Aldol addition (which has been a redirect to this page, way before this) or Aldol Condensation for more info.

That way confusion is prevented and we don't cause unnecessary overlap or maintenance.

I just don't see a way to avoid confusion otherwise. Since 'the aldol reaction' refers to the creation of an Aldol i.e the aldol addition reaction.

But then there also needs to be way to refer to the set of reactions, because they're interrelated.

For example if you attempt an Aldol addition but use significant heat you'll end up with aldol condensation product (or an impure mixture of the two depending on how sterically hindered your catalyst is).

Id prefer to not create a new page but given that both Aldol addition and Aldol condensation are deserving of their own pages, necessary given the wide breath of content for each and because of established, albeit clumsy, terminology thats aged in. I think these distinct pages are necessary. LoomCreek (talk) 07:07, 22 April 2023 (UTC)

You propose a split, or you're just going to do one and worry about getting consensus later? It seems like your editing is getting ahead of the discussion. And now you've also proposed to rename the page; doesn't that pre-suppose a split with the remnant here being moved to aldol addition? I suggest you lay off the editing for a while, at least of this article, and wait for people to have their say about what you propose. As mentioned, this is a longstanding article that nobody has had a major beef with, so it is far from obvious that there will be a consensus to carve it up. Lithopsian (talk) 15:39, 22 April 2023 (UTC)

@Lithopsian No I made a mistake. I promise I was not trying to do anything I thought would be controversial.

By the time I made them, ie the new page, I received messages from Michael Turnbull. Everyone else including admins had approved it but I held off on it (stopping the technical renaming process).

As for the moves, those sections were just wrong and don't belong in Aldol reaction. So either they should be deleted or moved to either Aldol condensation or the new page.

I'll do all the work to put everything back when the decision is reached. There's just no simple or easy way to do that in the meantime.

As for this page itself there were several explicit technical errors that needed to be fixed. With some reactions listed as condensation reactions (which require leaving groups, such as water) when they were not. Specifically the Crossed-aldol reactant control section, which wrongly listed them as condensation reactions, so I had to removed that labeling. LoomCreek (talk) 20:44, 22 April 2023 (UTC)

Requested move 21 April 2023

The following is a closed discussion of a requested move. Please do not modify it. Subsequent comments should be made in a new section on the talk page. Editors desiring to contest the closing decision should consider a move review after discussing it on the closer's talk page. No further edits should be made to this discussion.

The result of the move request was: no consensus. The main line of discussion here was WP:RECOGNIZABILITY, and participants were split on the question of whether the proposed title would be recognizable. (non-admin closure) ModernDayTrilobite (talk • contribs) 18:05, 8 May 2023 (UTC)

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Aldol reaction → Aldol addition – Aldol reaction (singular) refers to Aldol additions in English. While in other languages its referring to the general set of reactions. So for chemists who are fluent in English but it's not their first language (which is fairly common within Wikipedia chemistry) its caused some editing mistakes. The majority of the page is about aldol addition, but there were some sections about the overall pair of reaction which have since been moved to Aldol reactions. With only two mentions of aldol condensations kept where it explained how certain reaction conditions are necessary for Aldol additions (to avoid condensation). See above for more information Talk:Aldol reaction#Mistake in translation (Aldol reaction vs. reactions) LoomCreek (talk) 15:38, 21 April 2023 (UTC) — Relisting. SkyWarrior 22:11, 28 April 2023 (UTC)

Please note that there is now also an article called Aldol reactions. Mccapra (talk) 01:55, 22 April 2023 (UTC)

Note: WikiProject Chemistry has been notified of this discussion. SkyWarrior 22:11, 28 April 2023 (UTC)

Comment Aldol reactions is likely unattributed in-wiki copy from Aldol reaction. User:LoomCreek, if that's true, it's against wikipedia policy. DMacks (talk) 06:53, 29 April 2023 (UTC)

@DMacks Oh shoot thank you for letting me know, I genuinely thought I had attributed it. There are sections from it LoomCreek (talk) 06:55, 29 April 2023 (UTC)

This edit-summary is a good start. But important to also use {{Copied}} on each's talkpage. That way it's a permanently-visible marker (easy to overlook an edit-summary even before it gets pushed off the "most recent edits" of the history). DMacks (talk) 07:01, 29 April 2023 (UTC)

Oppose. The "bible" of organic chemistry in the US, "MARCH’S ADVANCED ORGANIC CHEMISTRY" 6th edition, mentions "Aldol reaction(s)" 190x. Zero mention of aldol addition, even in the index. I also have never heard the term. --Smokefoot (talk) 13:18, 29 April 2023 (UTC)

It's a reference to the reaction type which is addition. It is most definitely used even if it's less formal. But it has the added benefit of making the distinction of itself from Aldol condensation much clearer. And I'll note it is used in literature, for example: Solvent Polarity and Framework Hydrophobicity of Hf-BEA Zeolites Influence Aldol Addition Rates in Organic Media --LoomCreek (talk) 02:08, 1 May 2023 (UTC)

It's also directly mentioned in https://commons.wikimedia.org/wiki/File:Simple_aldol_reaction.svg one of the main photos for this page that has been up since 2014. --LoomCreek (talk) 19:34, 1 May 2023 (UTC)

The discussion above is closed. Please do not modify it. Subsequent comments should be made on the appropriate discussion page. No further edits should be made to this discussion.

Suggested Edit: Remove the "Chirality" shown on ketone α-carbon in example reaction.

At the top of the page, the very first reaction shown, the ketone reactant is drawn with the R' group receding into the page, and one of the hydrogens coming out of the page. There is no reason to show this molecule with this particular 3D structure - which misleadingly suggests that the reactant either has a tendency to exist in this conformation (it doesn't, the bond freely rotates), or that the α-carbon affects the chirality of the products(no chirality is shown in the products).

To be a chiral center, carbon needs to have four different constituents bonded to it, right? The α-carbon here has only three (two of its four constituents are hydrogen).

Also, the products are not shown as stereoselective, so the 3D structure of the reagents shouldn't matter here.

Organic chemistry is not an area where I have a high level of subject-matter expertise, so I'm posting this for discussion in case I'm mistaken, or if there is some sort of convention to show the 3D structure like this even though it isn't fixed. 1MathematicalGuy (talk) 22:55, 9 July 2024 (UTC)

@1MathematicalGuy:. Good points. Sometimes this art is legacy stuff. Sometimes it is some amateur trying to show off. All kinds of stuff going on, for which we rely on people like you to highlight.--Smokefoot (talk) 23:05, 9 July 2024 (UTC)

Eventual split of beef-up

Some aldol reactions are practiced on a massive scale. Then there are cross aldol reactions mediated by many elegant B and Si and heterocyclic reagents. Academic chemists study that area, but the application of such methodology, at least on scale, is not mentioned. Maybe it is not used. Most of this article is about this "useless" methodology. So, maybe eventually, we build up the real-world portion of this article, spin-off the fancy reagent part, or find some real apps for the fancy reagents.--Smokefoot (talk) 17:57, 29 November 2024 (UTC)